P
US4053607AExpiredUtilityPatentIndex 91

Aryloxypyridine for treating hyperglycaemia

Assignee: BEECHAM GROUP LTDPriority: Apr 4, 1972Filed: Jun 13, 1975Granted: Oct 11, 1977
Est. expiryApr 4, 1992(expired)· nominal 20-yr term from priority
Inventors:THORNE DAVID EDWARDENGEL KURT
C07D 213/63C07D 213/30
91
PatentIndex Score
51
Cited by
1
References
47
Claims

Abstract

Compounds of the formula ##STR1## wherein Py is a substituted or unsubstituted 2-, 3- or 4-pyridyl, N-oxidized or quaternized pyridyl group; A is a group of the formula -- ALK--0 -- -- O--ALK -- -- ALK--O--Alk -- wherein Alk is straight or branched chain alkylene of 1 to 6 carbon atoms; R 1 is a carboxylic acid group, a group which is converted in the human body to a carboxylic acid group or acyl; R 2 , r 3 and R 4 are each hydrogen, a carboxylic acid group, a group which is converted in the human body to a carboxylic acid group, acyl, hydroxy, alkoxy, aralkoxy, aryloxy, an esterified hydroxy group, nitro, halogen or amino; May be formulated into pharmaceutical compositions useful for the treatment of hyperglycaemia by combining said compounds with a pharmaceutically acceptable non-toxic inert diluent or carrier.

Claims

exact text as granted — not AI-modified
We claim: 
     
       1. A pharmaceutical composition for the treatment of hyperglycaemia in humans in the form of a beverage, foodstuff, tablet, linguet, powder, capsule, slurry, troche, lozenge or syrup or in a form suitable for administration to humans which comprises a blood sugar lowering amount of a compound of the formula ##STR17## or a pharmaceutically-acceptable, non-toxic acid addition salt thereof, wherein Py is 2-, 3- or 4-pyridyl unsubstituted or substituted by lower alkyl; A is a group of the formula ##STR18## wherein ALK is straight or branched chain alkylene of 1 to 6 carbon atoms; R 1  is a carboxylic acid group or a group which is converted in the human body to a carboxylic acid group; and R 2 , R 3 , and R 4  are each hydrogen, a carboxylic acid group, a group which is converted in the human body to a carboxylic acid group, lower alkanoyl, hydroxyl, lower alkoxy, hydroxymethyl, nitro, halo or amino, provided that R 1  is not methyl, cyano, or methoxycarbonyl when Py is 2-pyridyl or 5-ethylpyridyl-2-yl and A is --O-CH 2  -- and R 2 , R 3  and R 4  are hydrogen or halo, in combination with a pharmaceutically-acceptable non-toxic, inert diluent or carrier therefor.   
     
     
       2. A pharmaceutical composition according to claim 1 wherein the compound is of the formula ##STR19## or a pharmaceutically acceptable, nontoxic acid addition salt thereof, wherein Py is 2-, 3- or 4-pyridyl unsubstituted or substituted in the meta- or para-position by lower alkyl; A is a group of the formula ##STR20## wherein ALK is straight chain alkylene of 1 to 6 carbon atoms and R a  and R b  are each hydrogen, a carboxylic acid group, lower alkyl having an odd number of carbon atoms or lower alkyl having an even number of carbon atoms and carrying a carboxylic acid substituent, at least one of R a  and R b  not being hydrogen; provided that when Py is 2-pyridyl or 5-ethypyrid-2-yl and A is --O--CH 2  --, neither R a  nor R b  is methyl or methoxycarbonyl. 
     
     
       3. A pharmaceutical composition according to claim 2 wherein ALk is straight-chain alkylene of 1 to 3 carbon atoms. 
     
     
       4. A pharmaceutical composition according to claim 1 wherein the compound is 4-n-propylphenoxy-2'-pyridylmethane, or a pharmaceutically-acceptable, nontoxic acid addition salt thereof. 
     
     
       5. A pharmaceutical composition according to claim 1 wherein the compound is 4-methylbenzyloxy-2'-pyridylethane, or a pharmaceutically-acceptable, nontoxic acid addition salt thereof. 
     
     
       6. A pharmaceutical composition according to claim 1 wherein the compound is 1-(4-methylbenzyloxy)-3'-(2'-pyridyl) n-propane, or a pharmaceutically-acceptable, nontoxic acid addition salt thereof. 
     
     
       7. A pharmaceutical composition according to claim 1 wherein the compound is 4-hydroxymethyl-phenoxy-2'-pyridylmethane, or a pharmaceutically-acceptable, nontoxic acid addition salt thereof. 
     
     
       8. A pharmaceutical composition according to claim 1 wherein the compound is 4-carboxyphenoxy-2'-pyridylmethane or a pharmaceutically-acceptable, nontoxic acid addition salt thereof. 
     
     
       9. A pharmaceutical composition according to claim 1 wherein the compound is 4-carboxymethylphenoxy-2'-pyridylmethane, or a pharmaceutically-acceptable, nontoxic acid addition salt thereof. 
     
     
       10. A pharmaceutical composition according to claim 1 wherein the compound is 4-carboxyethylethylenephenoxy-2'-pyridylmethane, or a pharmaceutically-acceptable, nontoxic acid addition salt thereof. 
     
     
       11. A pharmaceutical composition according to claim 1 wherein the compound is 4-β-carboxyethylethylpheoxy-2'-pyridylmethane, or a pharmaceutically-acceptable, nontoxic acid addition salt thereof. 
     
     
       12. A pharmaceutical composition according to claim 1 wherein the compound is 4-carbamylphenoxy-2'-pyridylmethane or a pharmaceutically-acceptable, nontoxic acid addition salt thereof. 
     
     
       13. A pharmaceutical composition according to claim 1 wherein the compound is 4-carbamylphenoxy-3'-pyridylmethane or a pharmaceutically-acceptable, nontoxic acid addition salt thereof. 
     
     
       14. A pharmaceutical composition according to claim 1 wherein the compound is 4-carbamylphenoxy-4'-pyridylmethane, or a pharmaceutically-acceptable, nontoxic acid addition salt thereof. 
     
     
       15. A pharmaceutical composition according to claim 1 wherein the compound is 4-carboxyethylphenoxy-3'-pyridylmethane, or a pharmaceutically-acceptable, nontoxic acid addition salt thereof. 
     
     
       16. A pharmaceutical composition according to claim 1 wherein the compound is 3-(6-methyl)-pyridoxy-4'-methylphenylmethane, or a pharmaceutically-acceptable, nontoxic acid addition salt thereof. 
     
     
       17. A pharmaceutical composition according to claim 1 wherein the compound is 3-(6-methyl)-pyridoxy-4'-carboxyethylphenylmethane, of a pharmaceutically-acceptable, nontoxic acid addition salt thereof. 
     
     
       18. A pharmaceutical composition according to claim 1 wherein the compound is 4-carboxyethyl-phenoxy-2'-pyridylmethane or a pharmaceutically-acceptable, nontoxic acid addition salt thereof. 
     
     
       19. A pharmaceutical composition according to claim 1 wherein the compound is 3-carboxyethylphenoxy-4'-pyridylmethane or a pharmaceutically-acceptable, nontoxic acid addition salt thereof. 
     
     
       20. A method for the treatment of hyperglycaemia in humans which comprises orally or intraperitoneally administering to such human an amount of a composition according to claim 2 sufficient to lower the blood sugar of said human to the normal range. 
     
     
       21. A method for the treatment of hyperglycaemia in humans which comprises administering to such human an amount of a composition according to claim 3 sufficient to lower the blood sugar of said human to the normal range. 
     
     
       22. A method for the treatment of hyperglycaemia in humans which comprises administering to such human an amount of a composition according to claim 4 sufficient to lower the blood sugar of said human to the normal range. 
     
     
       23. A method for the treatment of hyperglycaemia in humans which comprises administering to such human an amount of a composition according to claim 5 sufficient to lower the blood sugar of said human to the normal range. 
     
     
       24. A method for the treatment of hyperglycaemia in humans which comprises administering to such human an amount of a composition according to claim 6 sufficient to lower the blood sugar of said human to the normal range. 
     
     
       25. A method for the treatment of hyperglycaemia in humans which comprises administering to such human an amount of a composition according to claim 7 sufficient to lower the blood sugar of said human to the normal range. 
     
     
       26. A method for the treatment of hyperglycaemia in humans which comprises administering to such human an amount of a composition according to claim 8 sufficient to lower the blood sugar of said human to the normal range. 
     
     
       27. A method for the treatment of hyperglycaemia in humans which comprises administering to such human an amount of a composition according to claim 9 sufficient to lower the blood sugar of said human to the normal range. 
     
     
       28. A method for the treatment of hyperglycaemia in humans which comprises administering to such human an amount of a composition according to claim 10 sufficient to lower the blood sugar of said human to the normal range. 
     
     
       29. A method for the treatment of hyperglycaemia in humans which comprises administering to such human an amount of a composition according to claim 11 sufficient to lower the blood sugar of said human to the normal range. 
     
     
       30. A method for the treatment of hyperglycaemia in humans which comprises administering to such human an amount of a composition according to claim 12 sufficient to lower the blood sugar of said human to the normal range. 
     
     
       31. A method for the treatment of hyperglycaemia in humans which comprises administering to such human an amount of a composition according to claim 13 sufficient to lower the blood sugar of said human to the normal rage. 
     
     
       32. A method for the treatment of hyperglycaemia in humans which comprises administering to such human an amount of a composition according to claim 14 sufficient to lower the blood sugar of said human to the normal range. 
     
     
       33. A method for the treatment of hyperglycaemia in humans which comprises administering to such human an amount of a composition according to claim 15 sufficient to lower the blood sugar of said human to the normal range. 
     
     
       34. A method for the treatment of hyperglycaemia in humans which comprises administering to such human an amount of a composition according to claim 16 sufficient to lower the blood sugar of said human to the normal range. 
     
     
       35. A method for the treatment of hyperglycaemia in humans which comprises administering to such human an amount of a composition according to claim 17 sufficient to lower the blood sugar of said human to the normal range. 
     
     
       36. A method for the treatment of hyperglycaemia in humans which comprises administering to such human an amount of a composition according to claim 18 sufficient to lower the blood sugar of said human to the normal range. 
     
     
       37. A method for the treatment of hyperglycaemia in humans which comprises administering to such human an amount of a composition according to claim 19 sufficient to lower the blood sugar of said human to the normal range. 
     
     
       38. A pharmaceutical composition according to claim 1 wherein the compound is 4-methylphenoxy-3'-pyridylmethane or a pharmaceutically-acceptable, nontoxic acid addition salt thereof. 
     
     
       39. A pharmaceutical composition according to claim 1 wherein the compound is ##STR21## or a pharmaceutically acceptable acid addition salt thereof. 
     
     
       40. A pharmaceutical composition according to claim 39 which is in unit dosage form, each dosage unit containing from 0.1 to 20 mg of 4-carboxyethylphenoxy-2'-pyridylmethane or the equivalent amount of an acid addition salt thereof. 
     
     
       41. A method for the treatment of hyperglycaemia in humans which comprises administering to such human an amount of a composition according to claim 38 sufficient to lower the blood sugar of said human to the normal range. 
     
     
       42. A method for the treatment of hyperglycaemia in humans which comprises administering such human an amount of a composition according to claim 39 sufficient to lower the blood sugar of said human to the normal range. 
     
     
       43. A method for the treatment of hyperglycaemia in humans which comprises administering to such human an amount of a composition according to claim 40 sufficient to lower the blood sugar of said human to the normal range. 
     
     
       44. A method for the treatment of hyperglycaemia in humans which comprises administering to such human a hypoglycaemically effective amount of a composition according to claim 1 sufficient to lower the blood sugar of said human to the normal range. 
     
     
       45. A method for the treatment of hyperglycaemia in humans, which comprises administering to such human a hypoglycaemically effective amount of 4-carboxyethyl-phenoxy-2'-pyridylmethane or a pharmaceutically acceptable non-toxic acid addition salt thereof. 
     
     
       46. A method according to claim 45 wherein from 1.5-30 mg/kg per day of 4-carboxyethylphenoxy-2'-pyridylmethane is administered either as the free base or as a pharmaceutically acceptable non-toxic acid addition salt thereof. 
     
     
       47. A method according to claim 45 wherein the administration is oral.

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